That pierce pin looks normal. The pierce pin piece on the older ones like that "wiggle" around on the cup. The chamber plug is what keeps them straight.
That one looks like a PPS seal? I'd say try a harder seal. The stock sheridan seals are a fairly hard urethane and I don't even think you could get them to bend like that. Also, didn't I send you some recently? Try one of the "hard" seals in there.
I wasn't aware Mike (CCI) sold sheridan size seals?? The nelson ones are a bit smaller and would fall right out on a sheridan. Not sure what material he uses for the 12g changer seals but it's hard stuff. Definitely the hardest material of the bunch.